Hydrogen Peroxide → 3-[4-(3-Benzyloxyphenyl)-2-oxo-pyrrolidin-1-yl]benzamide

HRID 1727149Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]2[CH2:19][N:18]([C:20]3[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=3)[C:23]#[N:24])[C:17](=[O:28])[CH2:16]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:29].[Na+].OO>CCO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:15]2[CH2:19][N:18]([C:20]3[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=3)[C:23]([NH2:24])=[O:29])[C:17](=[O:28])[CH2:16]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 3-[4-(3-benzyloxyphenyl)-2-oxo-pyrrolidin-1-yl]benzonitrile (1.3 g, 3.36 mmol) in 25 mL EtOH was added 25% NaOH (0.15 mL) followed by the slow addition of 1.5 mL H2O2 (30%). The reaction mixture was heated to 45° C. and stirred for 5 h. The mixture was then cooled down and concentrated under reduced pressure. The residue was dissolved in 100 mL EtOAc, washed with water and brine, dried over MgSO4 and concentrated again. The residue was purified by column chromatography on silica gel (EtOAc:Hexane=1:3) to give 1.3 g of the desired product. Yield: 99%.

Workup

temperatureThe mixture was then cooled down
concentrationconcentrated under reduced pressure
dissolutionThe residue was dissolved in 100 mL EtOAc
washwashed with water and brine
dry with materialdried over MgSO4
concentrationconcentrated again
customThe residue was purified by column chromatography on silica gel (EtOAc:Hexane=1:3)

Sources & evidence

ORD record: ord-b9a5f8e27ecc46fea7c7513b67f2a5f9
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495016B2

Reaction notes

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